Allyl propyl disulfide

Last updated
Allyl propyl disulfide
Allyl propyl disulfide.png
Names
Preferred IUPAC name
3-(Propyldisulfanyl)prop-1-ene
Other names
2-Propenyl propyl disulphide
4,5-Dithia-1-octene [1]
Onion oil [1]
2-Propenyl propyl disulfide [1]
Propyl allyl disulfide [1]
1-Allyl-2-propyldisulfane (not recommended)
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.016.864 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 218-550-7
PubChem CID
RTECS number
  • JO0350000
UNII
UN number 1993
  • InChI=1S/C6H12S2/c1-3-5-7-8-6-4-2/h3H,1,4-6H2,2H3 Yes check.svgY
    Key: FCSSPCOFDUKHPV-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C6H12S2/c1-3-5-7-8-6-4-2/h3H,1,4-6H2,2H3
    Key: FCSSPCOFDUKHPV-UHFFFAOYAQ
  • S(SCCC)CC=C
Properties
C6H12S2
AppearancePale-yellow liquid
Odor strong onion-like odor [1]
Density 0.984 g/cm3
Melting point −15 °C; 5 °F; 258 K
Insoluble [1]
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Flash point 54.4 °C (129.9 °F; 327.5 K)
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 2 ppm (12 mg/m3) [1]
REL (Recommended)
TWA 2 ppm (12 mg/m3)
ST 3 ppm (18 mg/m3) [1]
IDLH (Immediate danger)
N.D. [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Allyl propyl disulfide is an organosulfur compound with the chemical formula C3H5S2C3H7. It is a volatile pale-yellow liquid with a strong odor. It is a major component of onion oil and is used in food additives and flavors. [2]

Allyl propyl disulfide is present in garlic and onion. When onion or garlic is sliced, the substance evaporates and causes eyes to irritate. [3] When garlic or onion is cooked, it also evaporates, ridding them of the spicy taste, and leaving a sweet taste.[ citation needed ]

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Diallyl disulfide is an organosulfur compound derived from garlic and a few other genus Allium plants. Along with diallyl trisulfide and diallyl tetrasulfide, it is one of the principal components of the distilled oil of garlic. It is a yellowish liquid which is insoluble in water and has a strong garlic odor. It is produced during the decomposition of allicin, which is released upon crushing garlic and other plants of the family Alliaceae. Diallyl disulfide has many of the health benefits of garlic, but it is also an allergen causing garlic allergy. Highly diluted, it is used as a flavoring in food. It decomposes in the human body into other compounds such as allyl methyl sulfide.

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Garlic allergy or allergic contact dermatitis to garlic is a common inflammatory skin condition caused by contact with garlic oil or dust. It mostly affects people who cut and handle fresh garlic, such as chefs, and presents on the tips of the thumb, index and middle fingers of the non-dominant hand. The affected fingertips show an asymmetrical pattern of fissure as well as thickening and shedding of the outer skin layers, which may progress to second- or third-degree burn of injured skin.

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References

  1. 1 2 3 4 5 6 7 8 9 NIOSH Pocket Guide to Chemical Hazards. "#0020". National Institute for Occupational Safety and Health (NIOSH).
  2. Lawson, Larry D.; Wang, Zhen Yu J.; Hughes, Bronwyn G. "Identification and HPLC quantitation of the sulfides and dialk(en)yl thiosulfinates in commercial garlic products" Planta Medica 1991, vol. 57, pp. 363-70. doi : 10.1055/s-2006-960119
  3. CDC - NIOSH Pocket Guide to Chemical Hazards